1. Round
26/09/2009 15:00 Selkirk FC - Preston Athletic FC 3:0
15:00 Clachnacuddin FC - Wick Academy FC 2:2
15:00 Auchinleck Talbot - Fort William FC 7:0
15:00 Nairn County FC - Golspie Sutherland 5:2
15:00 Edinburgh University AFC - Vale of Leithen FC 0:3
15:00 Inverurie Loco Works - St. Cuthbert Wanderers 5:0
15:00 Coldstream FC - Edinburgh City FC 1:5
15:00 Brora Rangers FC - Irvine Meadow XI 0:2
15:00 Buckie Thistle - Forres Mechanics FC 0:0
15:00 Whitehill Welfare - Wigtown & Bladnoch 1:1
15:00 Fraserburgh FC - Bonnyrigg Rose 1:1
15:00 Glasgow University - Girvan FC 1:4
15:00 Lossiemouth FC - Newton Stewart FC 4:1
15:00 Rothes FC - Banks O' Dee FC 1:5
15:00 Civil Service Strollers - Gala Fairydean 1:0
15:00 Hawick Royal Albert - Huntly FC 0:7
15:00 Dalbeattie Star - Keith FC 2:4
03/10/2009 15:00 Wick Academy FC - Clachnacuddin FC 2:1
15:00 Forres Mechanics FC - Buckie Thistle 1:4 pso
15:00 Wigtown & Bladnoch - Whitehill Welfare 0:3
15:00 Bonnyrigg Rose - Fraserburgh FC 1:2
2. Round
24/10/2009 15:00 Queen's Park FC - Livingston FC 1:3
15:00 Nairn County FC - Elgin City 2:4
15:00 Fraserburgh FC - Spartans FC 1:4
15:00 Deveronvale FC - Buckie Thistle 2:2
15:00 Whitehill Welfare - Threave Rovers 1:1
15:00 Inverurie Loco Works - Stranraer FC 2:1
15:00 Vale of Leithen FC - Keith FC 1:3
15:00 Forfar Athletic - East Stirlingshire FC 4:2
15:00 Cove Rangers - Annan Athletic 2:1
15:00 Selkirk FC - Irvine Meadow XI 0:3
15:00 Girvan FC - Wick Academy FC 1:4
15:00 Lossiemouth FC - Albion Rovers 0:2
15:00 Edinburgh City FC - Burntisland Shipyard 5:1
15:00 Banks O' Dee FC - Montrose FC 0:3
15:00 Huntly FC - Auchinleck Talbot 1:1
15:00 Civil Service Strollers - Berwick Rangers 1:2
31/10/2009 15:00 Threave Rovers - Whitehill Welfare 1:0
15:00 Auchinleck Talbot - Huntly FC 4:3
15:00 Buckie Thistle - Deveronvale FC 1:2 aet
3. Round
28/11/2009 13:30 Irvine Meadow XI - Arbroath FC 1:0
15:00 Airdrie United FC - Queen Of The South 4:0
15:00 Albion Rovers - Elgin City 1:0
15:00 Cowdenbeath FC - Alloa Athletic 0:0
15:00 Deveronvale FC - Ayr United 0:1
15:00 Edinburgh City FC - Keith FC 3:1
15:00 Montrose FC - East Fife FC 2:1
15:00 Greenock Morton FC - Dumbarton FC 0:0
15:00 Raith Rovers - Peterhead FC 0:0
15:00 Ross County FC - Berwick Rangers 5:1
15:00 Spartans FC - Forfar Athletic 0:1
15:00 Stirling Albion FC - Auchinleck Talbot 2:1
15:00 Threave Rovers - Inverurie Loco Works 1:2
15:00 Wick Academy FC - Brechin City FC 4:4
05/12/2009 15:00 Stenhousemuir FC - Cove Rangers 5:0
09/12/2009 19:45 Clyde FC - Livingston FC 1:1
01/12/2009 19:45 Peterhead FC - Raith Rovers 1:4
05/12/2009 15:00 Dumbarton FC - Greenock Morton FC 0:1
08/12/2009 19:45 Alloa Athletic - Cowdenbeath FC 1:0
19:45 Brechin City FC - Wick Academy FC 4:2
14/12/2009 19:45 Livingston FC - Clyde FC 7:1
4. Round
09/01/2010 15:00 St. Mirren FC - Alloa Athletic 3:1
15:00 Hibernian FC - Irvine Meadow XI 3:0
15:00 Aberdeen FC - Heart of Midlothian 2:0
15:00 Partick Thistle - Dundee United 0:2
10/01/2010 12:15 Hamilton Academical - Rangers FC 3:3
18/01/2010 19:45 Kilmarnock FC - Falkirk FC 1:0
19:45 Forfar Athletic - St. Johnstone FC 0:3
19:45 Albion Rovers - Stirling Albion FC 0:0
19:45 Ross County FC - Inverurie Loco Works 4:0
19:45 Inverness CT - Motherwell FC 2:0
19:45 Ayr United - Brechin City FC 1:0
19:45 Edinburgh City FC - Montrose FC 1:3
19/01/2010 19:45 Greenock Morton FC - Celtic FC 0:1
20/01/2010 19:45 Livingston FC - Dundee FC 0:1
25/01/2010 19:45 Raith Rovers - Airdrie United FC 1:1
19/01/2010 19:45 Rangers FC - Hamilton Academical 2:0 aet
20/01/2010 19:30 Stirling Albion FC - Albion Rovers 3:1
26/01/2010 19:30 Stenhousemuir FC - Dunfermline Athletic 1:2 aet
27/01/2010 19:45 Airdrie United FC - Raith Rovers 1:3
Round of 16
06/02/2010 12:30 St. Mirren FC - Rangers FC 0:0
15:00 St. Johnstone FC - Dundee United 0:1
15:00 Hibernian FC - Montrose FC 5:1
15:00 Kilmarnock FC - Inverness CT 3:0
15:00 Dundee FC - Ayr United 2:1
15:00 Raith Rovers - Aberdeen FC 1:1
15:00 Ross County FC - Stirling Albion FC 9:0
07/02/2010 12:15 Dunfermline Athletic - Celtic FC 2:4
16/02/2010 19:45 Aberdeen FC - Raith Rovers 0:1
17/02/2010 19:45 Rangers FC - St. Mirren FC 1:0
Quarter-finals
13/03/2010 12:15 Kilmarnock FC - Celtic FC 0:3
14:00 Hibernian FC - Ross County FC 2:2
15:00 Dundee FC - Raith Rovers 1:2
14/03/2010 12:05 Rangers FC - Dundee United 3:3
23/03/2010 19:45 Ross County FC - Hibernian FC 2:1
24/03/2010 19:45 Dundee United - Rangers FC 1:0
Semi-finals
10/04/2010 12:15 Celtic FC - Ross County FC 0:2
11/04/2010 15:00 Dundee United - Raith Rovers 2:0
Final
15/05/2010 15:00 Ross County FC - Dundee United 0:3 (0:0)